Is AI the new cigarettes? Our VC panel digs into Anthropic’s S-1 | E2356

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Today’s show:

Anthropic’s S-1 is here, and finally, we can start to develop a real understanding for the AI economy and whether the numbers add up. Anthropic shows an operating profit, a mostly non-cash $80.7 billion loss, and customers spending a shocking 9x what they were spending on intelligence just one year ago.

Is this the greatest business in history? Is AI now as addictive to enterprises as cigarettes once were to impressionable teens?

On this week’s VC Roundtable, Jason Calacanis is joined by D.A. Wallach (Time BioVentures), Dave McClure (Practical Venture Capital), and Ben Black (Akkadian Ventures / Powerlaw Corp.) to seek some answers.

They dig into the numbers, including that wild 900% net revenue retention, and consider how retail investors will consider the convertible-note charge behind their $80B loss. Plus they’ll debate whether Anthropic’s founders are really true believers driven by religious fervor, and if so, whether they’re destined to be out-competed by “rabid capitalists.”

Guests

D.A. Wallach on X:x.com/dawallach

Time BioVentures:timebioventures.com

Dave McClure on X:x.com/davemcclure

Practical Venture Capital:practicalvc.com

Trading Places podcast:youtube.com/@PracticalVentureCapital

Ben Black on LinkedIn:linkedin.com/in/benblack

Akkadian Ventures:akkadian.vc

Powerlaw Corp:pwrl.com

Relevant Links

Anthropic’s S-1, by the numbers (Fortune):fortune.com/2026/10/27/anthropic-s1-ipo-filing…

900% NRR and an $80.7B loss that mostly ins’t (HackerNoon):hackernoon.com/anthropics-s-1-shows-163b-in-ha… (hackernoon.com/anthropics-s-1-shows-$163b-in-h…)

Tickertrends:tickertrends.io

Replit makes OpenAI its default (TechCrunch):techcrunch.com/2026/10/17/replit-is-no-longer-…

Dario Amodei warns that rivals’ spending could risk bankruptcy (Fortune):fortune.com/2026/02/14/anthropic-ceo-dario-amo…

Machines of Loving Grace (Dario Amodei):darioamodei.com/essay/machines-of-loving-grace

Palantir CTO Shyam Sankar says AI researchers are taking up smoking (Fortune):fortune.com/2026/10/13/palantir-cto-shyam-sank…

Microsoft offers its first-ever voluntary buyouts (TechSpot):techspot.com/news/112174-microsoft-offers-volu…

Canva ranks among the top consumer AI apps (SmartCompany):smartcompany.com.au/artificial-intelligence/ca…

SpaceX Q3: Musk says it could rent out its AI compute several times over (Constellation Research):constellationr.com/insights/news/spacexs-q3-mu…

Jason’s 2026 “Bitcoin is Dead” post:x.com/Jason/status/2114956980674605075

Jason to Michael Saylor: "there are better places to invest your money”:x.com/Jason/status/2115274438979756346

Timestamps:

0:00 Anthropic files its public S-1

4:58 Anthropic vs. OpenAI revenue run rates

9:20 PayPal is built for all businesses. Get started at paypal.com/business

10:02 “The greatest business in the history of capitalism”

11:58 Is intelligence the new tobacco?

18:08 The “meat sack constraint”

20:36 Thanks to our partner, The Conservation Fund! Learn more at conservationfund.org

22:13 Plaud: If your work depends on conversations - interviews, meetings, calls - you need a Plaud NotePin S. You can check it out at plaud.ai/twist and use code TWIST for 10% off!

24:32 The Who Has the Most Subscribers Challenge

28:08 Is Apple waiting out the AI race on purpose

30:22 Hostinger: The all-in-one platform for domains, websites, email, and marketing. Go to hostinger.com/twist and use the code TWIST for an additional 10% off Black Friday and Cyber Monday

34:19 Is Canva an AI company?

39:08 True Believers who still want to make money

48:21 The $72.4B convertible-note charge, explained

51:03 How long does AI compute stay useful?

58:19 Jason’s monthly “Bitcoin is Dead” post

1:04:41 Alicorns are unicorns with pegasus wings

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